The 10 Most Unsettling Dark Comedies of All Time

There’s something about modern life that calls for dark humor. It seems appropriate that, in the face of adversities, the best form of defense is to poke fun at those very adversities through the time-honored American tradition of celebrating the macabre, the unsettling and the downright twisted. Here at “PopCrunch Towers” we decided to put together a list of the ten black comedies that made us feel the most genuinely uncomfortable; menacingly comic cinematic milestones that managed to be by turns â€” or at once â€” both funny and disturbing. So get your cringe muscles tensed, and we’ll begin!

10. Grosse Pointe Blank

The 1997 George Armitage movie Grosse Pointe Blanke is something of a cult classic. This truly dark comedy portrays the existential crisis of a professional assassin returning to his hometown for a high school reunion. This movie has it all: guns, death, more death, and the non-ironic use of comedic one-liners. But it’s something much deeper that gives this film its unsettling edge. The believability of John Cusack’s hitman gives the lead character a personality that is easy to relate to. We find ourselves recoiling in discomfort at the recognizable mental traumas he faces regarding his morally ambiguous career choice. Like someone who works at McDonald’s.